tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → 4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][C:21]3[N:20]=[CH:19][C:18]4=[CH:17][CH:16]=[C:15]([C:11]5[CH:12]=[CH:13][CH:14]=[C:9]([S:6](=[O:7])(=[O:8])[NH:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH:10]=5)[N:23]4[N:22]=3)=[CH:40][CH:39]=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]Participants
3
Procedure
4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from N-tert-butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide and 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester in an analogous manner to Example 1052a. Product isolated as an orange foam (82 mg, 47%). LCMS (m/e) 627 (M+Na); 1H-NMR (CDCl3, 400 MHz) δ 8.79 (s, 1H), 8.74 (s, 1H), 8.29 (d, 1H, J=8.1 Hz), 7.87 (d, 1H, J=7.9 Hz), 7.62-7.53 (m, 3H), 7.31-7.24 (m, 2H), 7.08 (d, 1H, J=4.8 Hz), 6.88-6.80 (m, 2H), 4.46 (s, 1H), 4.37-4.18 (m, 2H), 2.89-2.75 (m, 2H), 2.75-2.60 (m, 1H), 1.90-1.81 (m, 2H), 1.71-1.60 (m, 2H), 1.49 (s, 9H), 1.17 (s, 9H).
Sources & evidence
- ORD record
- ord-7e207e58aece41d7815807231e4d840b
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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